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Chemistry

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Also known as: 1474034-05-3, Rta-408, Rta 408, Nrf1-activator-1, Omaveloxolone [inn], Rta408
Molecular Formula
C33H44F2N2O3
Molecular Weight
554.7  g/mol
InChI Key
RJCWBNBKOKFWNY-IDPLTSGASA-N
FDA UNII
G69Z98951Q

Omaveloxolone
Omaveloxolone is a member of the synthetic oleanane triterpenoid class of compounds and an activator of nuclear factor erythroid 2 [NF-E2]-related factor 2 (Nrf2, Nfe2l2), with potential chemopreventive activity. Upon administration, omaveloxolone activates the cytoprotective transcription factor Nrf2. In turn, Nrf2 translocates to the nucleus, dimerizes with a small Maf protein (sMaf), and binds to the antioxidant response element (ARE). This induces the expression of a number of cytoprotective genes, including NAD(P)H quinone oxidoreductase 1 (NQO1), sulfiredoxin 1 (Srxn1), heme oxygenase-1 (HO1, HMOX1), superoxide dismutase 1 (SOD1), gamma-glutamylcysteine synthetase (gamma-GCS), thioredoxin reductase-1 (TXNRD1), glutathione S-transferase (GST), glutamate-cysteine ligase catalytic subunit (Gclc) and glutamate-cysteine ligase regulatory subunit (Gclm), and increases the synthesis of the antioxidant glutathione (GSH). Nrf2, a leucine zipper transcription factor, plays a key role in the maintenance of redox balance and cytoprotection against oxidative stress.
1 2D Structure

Omaveloxolone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
N-[(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,14a,14b-decahydropicen-4a-yl]-2,2-difluoropropanamide
2.1.2 InChI
InChI=1S/C33H44F2N2O3/c1-27(2)11-13-33(37-26(40)32(8,34)35)14-12-31(7)24(20(33)17-27)21(38)15-23-29(5)16-19(18-36)25(39)28(3,4)22(29)9-10-30(23,31)6/h15-16,20,22,24H,9-14,17H2,1-8H3,(H,37,40)/t20-,22-,24-,29-,30+,31+,33-/m0/s1
2.1.3 InChI Key
RJCWBNBKOKFWNY-IDPLTSGASA-N
2.1.4 Canonical SMILES
CC1(CCC2(CCC3(C(C2C1)C(=O)C=C4C3(CCC5C4(C=C(C(=O)C5(C)C)C#N)C)C)C)NC(=O)C(C)(F)F)C
2.1.5 Isomeric SMILES
C[C@@]12CC[C@]3(CCC(C[C@H]3[C@H]1C(=O)C=C4[C@]2(CC[C@@H]5[C@@]4(C=C(C(=O)C5(C)C)C#N)C)C)(C)C)NC(=O)C(C)(F)F
2.2 Other Identifiers
2.2.1 UNII
G69Z98951Q
2.3 Synonyms
2.3.1 MeSH Synonyms

1. N-(11-cyano-2,2,6a,6b,9,9,12a-heptmethyl-10,14-dioxo-1,3,4,5,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2h-picen-4a-yl)-2-2-difluoropropionamide

2. Rta 408

3. Rta-408

2.3.2 Depositor-Supplied Synonyms

1. 1474034-05-3

2. Rta-408

3. Rta 408

4. Nrf1-activator-1

5. Omaveloxolone [inn]

6. Rta408

7. G69z98951q

8. N-[(4as,6ar,6bs,8ar,12as,14ar,14bs)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,14a,14b-decahydropicen-4a-yl]-2,2-difluoropropanamide

9. Propanamide, N-(2-cyano-3,12-dioxo-28-noroleana-1,9(11)-dien-17-yl)-2,2-difluoro-

10. N-(2-cyano-3,12-dioxo-28-noroleana-1,9(11)-dien-17-yl)-2,2-difluoropropanamide

11. Unii-g69z98951q

12. Omaveloxolone (usan/inn)

13. Omaveloxolone [usan]

14. Omaveloxolone [who-dd]

15. Gtpl7573

16. Chembl4303525

17. Schembl15349371

18. Ex-a541

19. Dtxsid101138251

20. Bcp28609

21. Mfcd28167769

22. Akos037648676

23. Zinc144682962

24. Db12513

25. Bs-15146

26. Hy-12212

27. N-(11-cyano-2,2,6a,6b,9,9,12a-heptmethyl-10,14-dioxo-1,3,4,5,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2h-picen-4a-yl)-2-2-difluoropropionamide

28. D10964

29. Rta408; Rta408; Rta-408;nrf1-activator-1

30. Q21098900

31. N-((4as,6ar,6bs,8ar,12as,14ar,14bs)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-octadecahydropicen-4a-yl)-2,2-difluoropropanamide

2.4 Create Date
2013-11-18
3 Chemical and Physical Properties
Molecular Weight 554.7 g/mol
Molecular Formula C33H44F2N2O3
XLogP36.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass554.33199959 g/mol
Monoisotopic Mass554.33199959 g/mol
Topological Polar Surface Area87 Ų
Heavy Atom Count40
Formal Charge0
Complexity1320
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

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